The title compound 3-methyl-l-（4-methylphenyl）-4-（N-4-trifluoromethylphenyl） aminomethyl-5-（4-methoxyphenylthio）-lH-pyrazole has been synthesized via a four-step reaction and characterized by IR, 1H NMR, element...The title compound 3-methyl-l-（4-methylphenyl）-4-（N-4-trifluoromethylphenyl） aminomethyl-5-（4-methoxyphenylthio）-lH-pyrazole has been synthesized via a four-step reaction and characterized by IR, 1H NMR, elemental analysis and X-ray crystallography. The compound crystallizes in monoclinic, space group P21/c with a = 8.7170（15）, b = 18.355（3）, c = 15.292（3） A, fl = 103.445（3）°, V= 2379.7（7） A3, Dc = 1.350 g/cm3, Z = 4, p = 0.184, F（000） = 1008, and the final R = 0.0491 and wR = 0.1339 for 4160 observed reflections （I 〉 2a（/））. The results demonstrate that there is a face-to-face π-π stacking interaction between one benzene ring （C（19）-C（24）） and another （C（I 3）-C（! 8）） at a plane-plane distance of 3.3539 A. The ring normal and vector between the ring centroids form an angle of 18.2° up to the centroid-to-centroid distance of 3.5273 A. The crystal structure is stabilized by the intermolecular hydrogen bond of N（3）-H（3A）...N（2） （symmetry code： A -x＋l, -y＋l, -z）. The preliminary biological test shows that the title compound has a moderate antifungal activity.展开更多
The title compound N-（（2,6-difluorophenyl）carbamoyl）-1,3-dimethyl-1 H-pyrazole-4-carboxamide（C13H12F2N4O2） was synthesized, and its structure was confirmed by ^1H NMR,HRMS and X-ray diffraction. It crystallizes ...The title compound N-（（2,6-difluorophenyl）carbamoyl）-1,3-dimethyl-1 H-pyrazole-4-carboxamide（C13H12F2N4O2） was synthesized, and its structure was confirmed by ^1H NMR,HRMS and X-ray diffraction. It crystallizes in the monoclinic system, space group P21/c with a = 9.50（2）, b = 10.11（2）, c = 14.07（3） A^°, β = 102.15（3）°, Dc = 1.480 g/cm^3, Z = 4, V = 1320（5） A^°3, the final R = 0.0789 and wR = 0.1860 for 1054 observed reflections with I 〉 2σ（I）. The preliminary biological test shows that the title compound has weak antifungal activities.展开更多
Compounds 1 （C15H17C1F3N303, Mr = 379） and 2 （C14H14C1F3N4OS, Mr = 378） have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction. Crystal 1 belongs to the triclinic sy...Compounds 1 （C15H17C1F3N303, Mr = 379） and 2 （C14H14C1F3N4OS, Mr = 378） have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction. Crystal 1 belongs to the triclinic system, space group P1 with a = 6.0223（19）, b = 9.324（3）, c = 15.936（5） A, a = 80.687（5）, β= 87.289（5）, ）, = 86.097（5）°, V= 880.4（5） A3, Z = 2, Dc = 1.433 g/cm3,μ（MoKa） = 0.266 mm^-1, F（000） = 392, R = 0.0861 and wR = 0.1999 for 2022 observed reflections with I 〉 2o（/）. Crystal 2 belongs to the triclinic system, space group PI with a = 7.7029（15）, b = 8.3371（16）, c = 14.410（3） A, a = 100.672（3）, β= 103.168（3）, ？ = 98.726（3）°, V = 876.1（3） A3, Z = 2, Dc= 1.451 g/cm^3,μ（MoKa） = 0.379 mm^-1, F（000） = 388, R = 0.0672 and wR = 0.2105 for 2725 observed reflections with I 〉 2σ（I）. Although the two compounds are similar with the same pyrazole and pyrethroid units, X-ray analysis reveals that their structures are completely different.展开更多
Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed,synthesized and characterized in detail via1 H NMR,^（13） C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of th...Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed,synthesized and characterized in detail via1 H NMR,^（13） C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani,Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC_（50） values of 0.013, 1.608 and 1.874 mg/m L, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC_（50） value of 22.21 mg/m L. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.展开更多
Pyrazole carboxamide derivatives represent an important class of fungicides in agrochemicals. To find more novel structural pyrazole carboxamides, a novel series of 3-（trifluoromethyl）-lH-pyrazole-4-carboxamide comp...Pyrazole carboxamide derivatives represent an important class of fungicides in agrochemicals. To find more novel structural pyrazole carboxamides, a novel series of 3-（trifluoromethyl）-lH-pyrazole-4-carboxamide compounds were prepared from ethyl 4,4,4-trifluoroace- toacetate and triethyl orthoformate as starting materials. All the products were characterized by Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance （NMR）, 13C NMR, 19F NMR and mass spectrography. The bioassay results showed these fluorine-containing pyrazole carboxamides have a weak fungicidal activity but some of them exhibit a good nematocidal activity against M. incognita.展开更多
A series of novel furan-1,3,4-oxadiazole carboxamide derivatives (5a~5e) were designed,synthesized and characterized by spectroscopic methods including HR-MS,^(1)H-and ^(13)C-NMR.The crystal structure of compound 5a w...A series of novel furan-1,3,4-oxadiazole carboxamide derivatives (5a~5e) were designed,synthesized and characterized by spectroscopic methods including HR-MS,^(1)H-and ^(13)C-NMR.The crystal structure of compound 5a was determined by single-crystal X-ray diffraction.The compound crystallizes in the triclinic system,space group P■ with a=4.7261(5),b=10.4672(11),c=14.5886(13)?,α=106.081(4)°,β=91.043(3)°,γ=99.456(4)°,Z=2,V=682.48(12)?^(3),M_(r)=348.16,D_(c)=1.694 Mg/m^(3),S=1.008,m=3.025 mm^(-1),F(000)=348,the final R=0.0775 and w R=0.2080 for 2774 observed reflections (I (29) 2σ(I)).There are two kinds of hydrogen bonds (N(3)–H(3A)×××N(2) and C(8)–H(8A)×××O(3)) present in its crystal structure.The preliminary antifungal assay showed that compounds 5b and 5c exhibited significant antifungal activities against several plant pathogenic fungi.展开更多
酰胺类化合物是最重要的农用杀菌剂之一.为了获得具有高抗植物病原真菌活性的新型酰胺类化合物,本论文设计、合成了20种结构新颖的含二芳胺结构的2-甲基-3呋喃甲酰胺类化合物,并通过了1 H NMR的结构确定.采用菌丝生长速率法对合成的化...酰胺类化合物是最重要的农用杀菌剂之一.为了获得具有高抗植物病原真菌活性的新型酰胺类化合物,本论文设计、合成了20种结构新颖的含二芳胺结构的2-甲基-3呋喃甲酰胺类化合物,并通过了1 H NMR的结构确定.采用菌丝生长速率法对合成的化合物进行抗四种植物病原真菌的活性测定,结果表明大部分化合物对油菜菌核病菌和水稻纹枯病菌表现出显著抑菌效果.化合物1i对油菜菌核病菌的EC50值为1.9229mg/L,优于商品杀菌剂啶酰菌胺(2.6736mg/L)和先导杀菌剂甲呋酰胺(9.9667mg/L),显示出较好的抗菌活性,为进一步以此类新型杀菌剂进行先导优化提供理论基础.展开更多
基金supported by Research Fund for the Doctoral Program of Zunyi Medical College(F-564)Natural Science Foundation of Guizhou Province(No.J2011[2083])
文摘The title compound 3-methyl-l-（4-methylphenyl）-4-（N-4-trifluoromethylphenyl） aminomethyl-5-（4-methoxyphenylthio）-lH-pyrazole has been synthesized via a four-step reaction and characterized by IR, 1H NMR, elemental analysis and X-ray crystallography. The compound crystallizes in monoclinic, space group P21/c with a = 8.7170（15）, b = 18.355（3）, c = 15.292（3） A, fl = 103.445（3）°, V= 2379.7（7） A3, Dc = 1.350 g/cm3, Z = 4, p = 0.184, F（000） = 1008, and the final R = 0.0491 and wR = 0.1339 for 4160 observed reflections （I 〉 2a（/））. The results demonstrate that there is a face-to-face π-π stacking interaction between one benzene ring （C（19）-C（24）） and another （C（I 3）-C（! 8）） at a plane-plane distance of 3.3539 A. The ring normal and vector between the ring centroids form an angle of 18.2° up to the centroid-to-centroid distance of 3.5273 A. The crystal structure is stabilized by the intermolecular hydrogen bond of N（3）-H（3A）...N（2） （symmetry code： A -x＋l, -y＋l, -z）. The preliminary biological test shows that the title compound has a moderate antifungal activity.
基金funded by Natural Science Foundation of Zhejiang Province(No.LY16C140007)National Natural Science Foundation of China(No.31401691)
文摘The title compound N-（（2,6-difluorophenyl）carbamoyl）-1,3-dimethyl-1 H-pyrazole-4-carboxamide（C13H12F2N4O2） was synthesized, and its structure was confirmed by ^1H NMR,HRMS and X-ray diffraction. It crystallizes in the monoclinic system, space group P21/c with a = 9.50（2）, b = 10.11（2）, c = 14.07（3） A^°, β = 102.15（3）°, Dc = 1.480 g/cm^3, Z = 4, V = 1320（5） A^°3, the final R = 0.0789 and wR = 0.1860 for 1054 observed reflections with I 〉 2σ（I）. The preliminary biological test shows that the title compound has weak antifungal activities.
基金supported by Hubei University of Technology,Science and Technology Department of Hubei Province(No.ZRY0981)National Natural Science Foundation of China(No.21272086)
文摘Compounds 1 （C15H17C1F3N303, Mr = 379） and 2 （C14H14C1F3N4OS, Mr = 378） have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction. Crystal 1 belongs to the triclinic system, space group P1 with a = 6.0223（19）, b = 9.324（3）, c = 15.936（5） A, a = 80.687（5）, β= 87.289（5）, ）, = 86.097（5）°, V= 880.4（5） A3, Z = 2, Dc = 1.433 g/cm3,μ（MoKa） = 0.266 mm^-1, F（000） = 392, R = 0.0861 and wR = 0.1999 for 2022 observed reflections with I 〉 2o（/）. Crystal 2 belongs to the triclinic system, space group PI with a = 7.7029（15）, b = 8.3371（16）, c = 14.410（3） A, a = 100.672（3）, β= 103.168（3）, ？ = 98.726（3）°, V = 876.1（3） A3, Z = 2, Dc= 1.451 g/cm^3,μ（MoKa） = 0.379 mm^-1, F（000） = 388, R = 0.0672 and wR = 0.2105 for 2725 observed reflections with I 〉 2σ（I）. Although the two compounds are similar with the same pyrazole and pyrethroid units, X-ray analysis reveals that their structures are completely different.
基金supported by National Key Research and Development Program of China(No.2016YFC0502004-2)Applied Basic Research Program of Sichuan Province(No.2014JY0063)
文摘Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed,synthesized and characterized in detail via1 H NMR,^（13） C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani,Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC_（50） values of 0.013, 1.608 and 1.874 mg/m L, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC_（50） value of 22.21 mg/m L. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.
文摘Pyrazole carboxamide derivatives represent an important class of fungicides in agrochemicals. To find more novel structural pyrazole carboxamides, a novel series of 3-（trifluoromethyl）-lH-pyrazole-4-carboxamide compounds were prepared from ethyl 4,4,4-trifluoroace- toacetate and triethyl orthoformate as starting materials. All the products were characterized by Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance （NMR）, 13C NMR, 19F NMR and mass spectrography. The bioassay results showed these fluorine-containing pyrazole carboxamides have a weak fungicidal activity but some of them exhibit a good nematocidal activity against M. incognita.
基金supported by the National Natural Science Foundation of China (31770616)the Natural Science Foundation for Colleges and Universities in Jiangsu Province (17KJA220002)。
文摘A series of novel furan-1,3,4-oxadiazole carboxamide derivatives (5a~5e) were designed,synthesized and characterized by spectroscopic methods including HR-MS,^(1)H-and ^(13)C-NMR.The crystal structure of compound 5a was determined by single-crystal X-ray diffraction.The compound crystallizes in the triclinic system,space group P■ with a=4.7261(5),b=10.4672(11),c=14.5886(13)?,α=106.081(4)°,β=91.043(3)°,γ=99.456(4)°,Z=2,V=682.48(12)?^(3),M_(r)=348.16,D_(c)=1.694 Mg/m^(3),S=1.008,m=3.025 mm^(-1),F(000)=348,the final R=0.0775 and w R=0.2080 for 2774 observed reflections (I (29) 2σ(I)).There are two kinds of hydrogen bonds (N(3)–H(3A)×××N(2) and C(8)–H(8A)×××O(3)) present in its crystal structure.The preliminary antifungal assay showed that compounds 5b and 5c exhibited significant antifungal activities against several plant pathogenic fungi.
文摘酰胺类化合物是最重要的农用杀菌剂之一.为了获得具有高抗植物病原真菌活性的新型酰胺类化合物,本论文设计、合成了20种结构新颖的含二芳胺结构的2-甲基-3呋喃甲酰胺类化合物,并通过了1 H NMR的结构确定.采用菌丝生长速率法对合成的化合物进行抗四种植物病原真菌的活性测定,结果表明大部分化合物对油菜菌核病菌和水稻纹枯病菌表现出显著抑菌效果.化合物1i对油菜菌核病菌的EC50值为1.9229mg/L,优于商品杀菌剂啶酰菌胺(2.6736mg/L)和先导杀菌剂甲呋酰胺(9.9667mg/L),显示出较好的抗菌活性,为进一步以此类新型杀菌剂进行先导优化提供理论基础.
